When a Man Meets a Robot
by wildstraydog
Summary: Jaune - socially awkward, clumsy, one of the weakest hunters in Vale. Penny - The first synthetic to produce an aura, a sheltered girl with few friends. What will happen when these two meet each other?
1. Chapter 1

When a Man Meets a Robot

By wildstraydog

Chapter One: The Gears begin to Turn

**Hey guys, I'm back! Like I said before I planned on writing a new story featuring our favorite robot girl Penny (Technically a synthetic)! **

**This new story will in no way change the schedule for **_**Catching a Snowflake**_**. Sorry if I upset any fans because of this, and please read and review. Boy is it hard to write for Penny.**

There he was, Jaune Arc, the klutz of Vale, balancing five bags of clothes, books, magazines, candy, and other supplies while trying not to fall. Jaune was still trying to figure out how he got in this peculiar situation. All he planned to do was go to Vale and walk around the city, get a little free time, but then the worst happened.

It took him all day to keep it a secret, the only person he told was Pyrrha so she wouldn't have to worry. When classes were over, he began to creep down the halls, avoiding the appearance of team RWBY. He somehow made it to the front entrance of Beacon Academy, all he needed to do was walk on over to the doors and sprint like a mad man.

Jaune made a classic sprinter pose, and began to count to three. 1...2...3, before he could dash, he felt a large soft hand grab his hood, causing him to fall to the ground, choking. When he looked up, he saw lilac eyes and a Cheshire grin.

It was Yang, and before he knew it, all the other girls from team RWBY surrounded him, he also saw Nora hiding behind Blake with a fire in her eyes. Yang found a small slip of paper on the ground and heard a small eep escape from Jaune, and she began to giggle. As the girls began to read, they realized it was a list of places Jaune planned to visit while in Vale.

Hence where Jaune's predicament resulted in him shopping for the girls, instead of enjoying his day out in the beautiful city of Vale, Jaune hated his life. He was already tired from running to place to place, and some of the purchases made him feel awkward, such as the pair of panties Yang wanted... Jaune didn't even want to think what the cashier thought.

Sore feet and an aching pain in his back, led him to one of the benches next to a fountain. He sat down and stretched, feeling the pain fade away, and looked around. It wasn't too busy, and he only saw a few students from Beacon around in some of the restaurants. Jaune fiddled with his scroll and saw it was 2:00, half of his planned day was gone, and he made a large sigh.

Jaune wasn't totally clueless, despite his demeanor. However it took several minutes for him to realize that he was not alone on the bench. He turned his head, and noticed a young girl with orange curly hair and a cute pink ribbon on the top. It took a moment for him to register, as he never saw her sit down.

Without thinking, Jaune scooted closer to the girl and began to take in her features. It wasn't in the creepy ogling type way, but more of curiosity. She had bright green eyes, small freckles, and light complexion. The girl wore a blouse with overalls, with a green and black collar that matched her stockings. Jaune felt a small blush appear, realizing how cute and close to her he was.

However that's when he noticed something off about her. She was staring straight, Jaune looked over and saw nothing of interest in her direction, and he began to scratch his cheek. The girl seemed out of it, so he decided to be brave and wave his hand in front of the girl. There was no reaction, and Jaune began to worry.

"Um, excuse me, are you ok?" He asked with a gentle voice. The girl's eyes sparkled and she slowly turned to face Jaune. He didn't know if he should be scared or glad.

"Well hello sir, it's a pleasure to meet you!" The girl jovially announced, extending her hand for Jaune to shake. He took the girls cold hands and began to shake. She had a firm grip.

"Uh, nice to meet you also, I'm Jaune, Jaune Arc, and I was just wondering if you were ok, you looked like you blanked out there." Jaune cursed himself for not adding a clever line with his introduction.

"My name is Penny, I was just admiring that little kitten over there by the Atlesian restaurant, aren't they so amusing?" She pointed and Jaune indeed saw a small black cat fiddling with rocks by the door.

"Oh wow, how did I not see that, I'm as clueless as ever huh?" Jaune sighed and picked up his bags, not wanting to bother Penny with his presence anymore. He stood up and wrapped the handles of the bags around his arms, beginning his balancing act so as not to spill everything.

"Wait Mr. Jaune, why do you have so many items?" Jaune stopped and turned around, he saw the innocent expression on her face and caved in, he couldn't ignore her, she looked so curious, like a child.

"A lot of my friends had me pick up some stuff, although I originally planned to spend the day alone. Funny how things turned out, I got to meet a cute girl because of it." Oh snap, Jaune thought as he finished his sentence. He couldn't believe he just blurted that out, he was such an idiot! Jaune was blushing like crazy and waving his heads around.

Penny just stared at him, as her mind calculated what response would be correct in this situation. A boy had just complimented her and called her "cute" so the correct response would be to thank him. As her gears turned, she began to think it over again, no boy had ever called her cute before. Penny was at a crossroad.

"I'm so sorry Penny. I didn't mean to upset you!" Jaune bowed as he apologized, dropping all of the bags onto the ground. He noticed his mistake and scrambled on all fours to clean his mess.

"Jaune...will you be my friend?" Penny asked. She looked up at Jaune, and he began to melt under her adorable bright green eyes. It wasn't that Jaune didn't want her to be his friend, not at all, he just felt so embarrassed.

"Yeah of course, I would like that."

"Jaune, that's...outstanding!" Penny yelled with joy, she jumped up and grabbed Jaune's hands, swinging him back and forth like a brand new doll she got for her birthday. Jaune's eyes appeared like spinning discs, and she set him down, unaware of his motion sickness.

Jaune covered his mouth and ran to the nearest trash can, spilling his guts. Penny tilted her head in confusion and pondered what could make the boy vomit so easily. It didn't matter. She skipped over to Jaune in glee and picked him up. Jaune wiped his mouth and found his balance again. After he composed himself, he began to blush, ashamed that he would vomit in front of such a beautiful girl.

"Oh Jaune, what she would do, there's so much to do in the city," Penny said, while clapping her hands. "We could visit the zoo, and eat at a fancy restaurant, or even hand glide!" Penny was speaking to fast for him, but he caught the hand glade part and shuddered.

"Uh, maybe we can do something more...relaxing?" Jaune thought of what they could do, he checked his scroll for the time and it read 2:30. He looked around and saw an ice-cream parlor. He grabbed Penny's cold smooth hand and dragged her across the street. When she looked up she became excited (For the record I don't know what Penny can eat).

"Excuse me, two vanilla ice-creams please." Jaune asked the older gentleman. The man scooped up the vanilla and put them on two brown cones. He handed them to Jaune and gave him a classic wink.

"You two make a cute couple, have a nice day now." Jaune blushed and Penny stared at her ice-cream, observing the contents of the delicious sweet.

The two of them headed for a small park in the city, while Jaune had to balance five shopping backs and his vanilla ice-cream, not an easy task for any man. Jaune chuckled as he watched Penny take slow licks of the vanilla, savoring every taste, nodding in approval. They found another bench under a tree, the shade blocking the scorching sun of Remnant.

By the time he began to taste his treat, Penny had gobbled up the whole thing, licking her fingers. She turned to Jaune and gave a large thumbs-up. Jaune couldn't believe her, and he began to chuckle. Penny was unlike any he girl he had ever met, she was energetic, curious, and also awkward. He knew he was no Casanova himself. Weiss wouldn't have rejected him over thirty times if that was the case.

"Thank you so much for the tasty cream Jaune!" Penny said, with each word full of energy. It sometimes felt like she was trying too hard.

"It's called ice-cream Penny, and no problem, anything for a friend." Penny beamed, excitement flowing through her synthetic body, but for some reason, she felt happy when she was around Jaune, just like when she was with her father and uncle Ironwood. He was her new friend, the second friend she had made in Vale.

"So I'm really your friend Jaune, for real!" Jaune seemed confused from the question. Didn't he already say he was? Penny must have been really sheltered he thought, enough that she doubted herself and others. Jaune felt horrible for her, he grabbed both her shoulders and hugged her.

Penny's mind rushed through thousands of algorithms, trying to compute what Jaune was doing. Penny knew it was a form of human compassion, used for comforting others, or expressing one's love to another individual. Penny had to conclude what action to take next that would be the right response for the hug he gave her

Penny accepted the embrace and hugged him back, a large smile on her face. The only problem was that Jaune arms began to hurt, and the crushing power known as Penny wouldn't let go. It was getting harder for him to breathe, and he tried to poke Penny on the shoulder. It was no use, she had her eyes close, her imagination running wild.

"You have such strong hugs, like a bear!" Penny looked over and saw the panting Jaune, she let go and gasped, his chest heaving up and down. His hand was on his throat, and he tried to imagine how such a sweet girl could have such strength. Penny helped him up and dusted off his shirt.

"You sure are powerful for such a...tiny girl," Jaune said with a giggle mixed with a cough.

"Thank you, I'm always combat ready!" Penny said. She pumped her fist in the air, and Jaune rubbed the back of his head, blowing it off as some inside joke he didn't understand, unaware of how powerful Penny really was.

"It's 3:30, I better get going Penny, but here's my contact info. Just message me if you need something. I study at Beacon so I'm not far from Vale, and I'm even a team leader." Jaune tried to flex his muscles, but Penny just stared with a smile.

"It's been an astounding evening Jaune, I expect many more adventures to come." Jaune laughed and turned to left. He waved at Penny and made his way to the next air-ship. However, unknown to Jaune, the lovable synthetic was processing in her mind the past hour.

Penny was ecstatic, and she couldn't wait to tell uncle Ironwood about her escapades with the young blond man. It was her first boyfriend after all, that's what they were. When two people of the opposite sex find attraction to each other, they engage in activities that can include dinner, a movie, or affections of love.

Based on the information she was receiving, it was proper for the boy to message the woman back and propose an appropriate time and place for another engagement. Penny brought up a calendar and checked her available dates. She was free for most of the week, until the dance at Beacon Academy. Penny could only hope that uncle Ironwood would be happy.

When Jaune arrived back at Vale he had a large smile on his face, he enjoyed his time with Penny, and was hopeful they would meet again. He was at team RWBY's door and found it opened. Jaune saw Ruby and Nora playing rock-paper-scissors, while Blake read another new book on her bed, Yang was listening to some music, and Weiss was studying, well until they all saw him. His instincts told him to run, but he just stood there, sweating.

"Hey guys, I'm back from-" Before he could finish he was tackled to the ground, as the girls grabbed their bags and inspected the contents. Jaune could hear cheerful compliments as he got up from the ground.

"Sorry we used you Jaune, but boy did you deliver!" Yang said with a wink.

"It's no problem. I actually had a pretty good time." Jaune realized he shouldn't have said that, Yang caught on and she began to tease him.

"Ohhhhh really, did something happen while in Vale?"

"Oh Jaune did you get in a fight, I was in a fight once, it was me and thirty Beowolves," Nora continued to ramble on while they waited for him to answer.

"Well...to be honest, I met a girl." The room went silent, and they all screeched, except for Weiss and Blake as they dragged Jaune into their room by his arms. He wanted to escape, but he couldn't reach his scroll to alert Pyrrha or Ren.

"Alright fuss up blondie, who's the hot tamale?" Yang said, poking his chest like a detective. He heard Nora get excited when she heard tamale.

"Ok, well her name's Penny and-" Jaune stopped, he saw everyone go bug eye, even Weiss was shocked when she fell out of her chair. Blake slammed her book shut and began to snicker. Yang couldn't hold it in, and she began to laugh like a lunatic.

"Penny, orange hair Penny, why is that not surprising," Weiss said as the stood back up and dusted off her skirt.

"They would make a good pair." Blake added.

Unknown to the group, Ruby stood in the corner with a worried look on her face. It wasn't the shock that Jaune had met Penny, but that he might like her. It wasn't Jaune she worried about, it was her friend Penny. All she could wonder was, 'Did he know'?


	2. Fixing the Kinks

When a Man Meets a Robot

By wildstraydog

Chapter Two: Fixing the Kinks

**Hey guys, sorry about the slight delay for this story. It's a little harder to come up with ideas for this one, especially when writing for Penny, who is more difficult to write then I thought. **

**However I have finally figured out where to go with this story. RWBY belongs to Rooster Teeth and Monty, and please read and review!**

Ironwood was at his desk in the temporary apartment he had rented while in Vale. Tapping his fingers at the table and listening to an old record that made him relax. There were was some last minute business from Atlas that needed to be taken care of, and as much as he loved Penny, he couldn't concentrate with her around.

The last incident at the hangers made him worry, and he hadn't expected Penny to engage members of the White Fang, or a wanted criminal like Roman Torchwick. So despite his better judgment, he gave Penny permission to roam the city without his supervision, of course he told her to be cautious and to remain in the city until curfew.

The general was happy about one thing though. Out of the large mess that Penny became entangled with, she had made friends, a little huntress named Ruby Rose. Ironwood was very familiar with her uncle Qrow, with more stories then he liked to remember.

The door to his apartment slammed open, something akin to a grand trumpet blowing through the halls of the castle to announce their king. Penny liked grand entrances, adding to her innocence. She walked over to the couch and pulled out a small wire from her back, and plugged it in a small black cube with the Schnee logo on it. The cube began to vibrate and Penny giggled at the sudden jolt.

"I have returned uncle Ironwood!" Penny shouted with bravado.

"So you have Penny, how was your stroll today, get into any trouble like last time? I don't want to have to deliver bad news to your father." Ironwood grabbed a cup of coffee, the same brand as Ozpin, and sat across from Penny on a leather gray couch.

"It was wonderful, the city is so beautiful, and the shops are so interesting. I never knew they sold movies outside of theaters."

"Yes, Vale is a sight to behold, especially in contrast to the snowy mountains and hills of Atlas. They have always sold movies to the people after they are released in theaters, its common practice." Ironwood and Penny would always have a back and forth whenever she learned something new. It helped her adjust to new environments and add to her personality so she didn't seem strange to others, or at least not as strange.

"Uncle Ironwood, I saw the most pretty cat today, it was all black, and then I ran into this sweet boy named Jaune, today was so great!" Ironwood almost dropped his half-cup of coffee onto his lap. He began to mimic Penny as he reset his mind and tried to run through her sentence. Did she say she met a boy? He had been prepared for this day, but didn't expect it so soon.

"I hate to interrupt Penny, but did you say you met a young boy today in the city?" Penny stopped pumping her fists in the air and tilted her head.

"Yes, Mr. Jaune, he's such a sweet boy, he even hugged me! He's tall, blonde, a little messy for a boy, has some substantial muscle." Ironwood almost felt like gouging his eyes out, little Penny, the first synthetic to produce aura, was impressed by a boy, but was it genuine or just the programming? Ironwood would have to find out with more questioning.

"What else do you know about this...Jaune boy?"

"He attends Beacon Academy, and is one of the team leaders. I also believe his last name is Arc." That intrigued him, Arc, as in the famous Arc family, and he attended Beacon did he? Perhaps he would have a little chat with this boy, with Ozpin's permission of course.

"So what did you do with Mr. Arc today? How did you two even meet each other? Don't be shy with the details either Penny." Penny gave a salute and beamed another bright smile.

"Jaune wanted to make sure I was ok, and I was fine as can be. Then we talked and he hugged me, boy was he fluffy! Oh and we ate something called ice-cream too. Uncle Ironwood, do you approve of my boyfriend, I believe a parent-like figure must usually approve." Ironwood's eyes became empty, boyfriend...when did he become her boyfriend!?

There was no way he could tell Penny's father that she met a boy and became her boyfriend in one day, he would flip out. She was designed to be a weapon, not another teenage girl that ran on dust. She was asking his approval, and her little robotic pout was beginning to take its toll on him, so he decided to blurt something stupid out.

"Mr. Arc needs to meet me first before I can give any sort of approval Penny. Perhaps you can have the boy over for dinner someday..." Ironwood didn't even finish his sentence, before he realized his life had been signed away. How could he a general of Atlas, be reduced to having a dinner with a top secret weapons potential boyfriend?

"That would be absolutely fantastic uncle Ironwood! I'll message Jaune right away." Penny unplugged herself and walked over to her room. She pulled out her scroll and set it on her bed, bringing up Jaune's contact info. She began to type away a suitable greeting and invitation for dinner at her apartment. She couldn't imagine what fun a boyfriend could be.

Rubbing his temple with his fingers wasn't helping, Ironwood was done with coffee. The man needed whiskey now. Ironwood didn't have the strength to ask how she got his contact info, but what he could do was phone Ozpin. Ironwood needed to learn more about the boy who would be coming over for dinner. Not to mention he didn't know how to cook.

"Hello, Ozpin, we need to have a chat."

Jaune was down in the dumps, it was cliché, but he didn't know how else to describe how he felt. He was dragging his feet through the hall, slumping forward, and his eyes dead like a fish. Jaune thought he did ok, he got to meet a nice girl, they hung out, and he even gave her his number. The problem though, he had no idea of how to contact her.

The way Yang explained it to him after she laughed at his misfortunate, was that men were supposed to contact the girl for a date, not the women. He slammed his head on the table four or five times after that conversation in the cafeteria. Ruby patted him on the shoulder and Weiss just said, "I told you so", as if she knew he would mess up somehow.

To take away his sorrows, Jaune headed to his room to get an afternoon nap, it wasn't alone however, as he opened the door to find Ren and Pyrrha, both studying. The whole thing was weird to him, he couldn't see Nora, and he checked the closet to see if she was hiding in wait for Jaune to enter.

"Nora isn't here, she went with Ruby and the others to paint their nails and talk about boys," Ren said as he flipped another page.

"I thought Weiss would never agree to something like that?"

"Well, she was forced," Pyrrha said with a smile. She turned and faced Jaune. She could see he was depressed, having heard from Yang about his little blunder in Vale with a girl named Penny. By what she heard, Penny sounded like a nice young woman, especially if she was willing to look past Jaune's faults, not that she thought he had a lot.

"Don't mind me guys, I'm going to take a nap." Jaune climbed into his bed and covered himself with the blankets he brought from home, but Pyrrha wouldn't have it, she marched over and ripped them off, giving Jaune a motherly stare. Jaune didn't know if he should cower in fear.

"I won't have you moping around Beacon Jaune, now you gave this young girl your contact info correct?"

"Well, yeah, but that doesn't mean-" Pyrrha cut him off with a wag of her finger.

"Then chin up, I'm sure if this girl really likes you Jaune, she will contact you. Don't underestimate the power of love." Jaune became flustered, love, he wasn't in love with Penny, he just thought she was cute and fun.

"I don't know about love."

"You don't have to rush into anything Jaune, but if you ever need someone to talk to, don't hesitate to talk to your team. We're always here for you leader, now stop complaining and do something useful." Pyrrha slapped him on the back with her hand, and he tumbled over, Pyrrha apologized and helped the blonde back up.

"T-thanks Pyrrha, you're right, I shouldn't worry." They both became silent when a small beeping noise erupted in the room. Ren looked over and Jaune lifted up his arm. He opened up the message to see it was from Penny. He stood up in excitement and began to read the message.

_Good evening Mr. Jaune, it is I Penny! I thought it would be proper to wait at least one day before contacting you, as is traditional with male and female relationships. I would like to invite you over for dinner tomorrow night at my apartment, and please dress to impress~_

_ Salutations - Penny_

Pyrrha gave a small sweat brow as she read the letter with Jaune. The way the girl wrote made her seem somewhat eccentric, but it was the thought that counted right? She looked over to see Jaune shake with excitement, but he soon became nervous when he realized he had been invited over to her apartment for dinner.

"Oh crap, oh crap, Pyrrha what do I do, I've never been on a date before, let alone in a girl's apartment!" Jaune shouted.

"Calm down Jaune, I'm sure Ren can help you, he should be experienced in this." Pyrrha looked up at Ren and he tilted his head. Why was he the experienced one, just because Nora hung out with him all the time? Ren wasn't ignorant, he knew how to talk to girls and learned some techniques in courtship, but he was often too busy.

"All I can tell you Jaune is to be yourself, don't try and feign confidence or it will collapse on you like an avalanche. Try to keep the conversation alive, talk about your interests. That is all." Ren slammed his book and hopped onto his bed and rolled away from them.

"See Jaune, it's that simple." Pyrrha said with glee.

"I don't know...I'm not suave like Ren is," Jaune said. They both heard a chuckle over from Ren's bed, and he began to cough.

"Don't worry about that Jaune, Dr. Love is here." Their door busted opened and Yang entered the room, a suitable theme song playing in the background. She was wearing thick black glasses and lifted them with her finger, she oozed off intelligence.

"Dr. Love?" Both Pyrrha and Jaune said in unison.

"That's right. I got a P.H.D. in Romance and a M.D. in ass kicking! Now Jaune, if you want to impress Penny, it shouldn't be too hard. She's a sweet girl, and you just need to play on that." Yang Sat on Jaune's bed and began to write some things down on her pad.

Before "Dr." Yang could continue her diagnosis, Jaune received a call on his scroll. He took it out and was greeted by the face of Ozpin, sipping his coffee with a strange smile on his face.

"Mr. Arc, I need you to report to my office ASAP, I have a special visitor here who would like to meet you." Jaune was confused, special visitor? He began to wonder if it was one of his sisters, and gave a small gulp.

"I'll be right back guys." Jaune heard Yang pout and Pyrrha waved him goodbye as he walked to Ozpin's, scared of what was to come.

On the way, he spotted a large airship and several military vehicles parked outside, someone was putting on a grand show trying to intimidate someone. When he looked closer, he could see the Atlas insignia planted on the side of the airship. What would the Atlas military be doing here he wondered?

Jaune arrived, he gave a light knock and entered Ozpin's office, and it was still as large as he remembered. He walked up to Ozpin who offered him a seat, still a small little smile on his lips. Jaune heard another set of footsteps from behind, and before he could turn around, a large muscular hand grabbed his shoulder. Jaune looked up and saw an imposing figure standing over him, a look of disapproval on his face.

"Hello Mr. Arc, I am General Ironwood."


	3. Inspecting the Hardware

When a Man Meets a Robot

By wildstraydog

Chapter Three: Inspecting the Hardware

**Hey guys, thanks for all the support for this strange pairing. You guys have helped me through the writer's block and I got the story now mapped out in my head. Now please continue the adventures of Jaune and Penny! RWBY belongs to Rooster Teeth and Monty Oum. please read and review, and thank you for the continued support.**

When a small rodent or animal comes face to face with its predator, it becomes full of fear, cowering before the massive beast that could result in its death. Jaune had no idea what to expect when a large hand gripped his shoulder from behind, but when he turned his head, all the color vanished from his face.

The reaper of death stood before him, a large malignant aura surrounding the man, small beady reds staring into his soul, ready to devour him. This illusion faded when Ozpin coughed, and Jaune gulped before the man in the uniform. Jaune pleaded with Ozpin with his eyes, but he only smiled and stood up from his chair, coffee mug in hand.

"I'll leave you two alone to talk, just go easy on him James." Ozpin waved goodbye to Jaune and left his office. It was a death sentence, he had been beckoned to the guillotine by Ozpin, thrown to the proverbially wolves. He expected his life to flash before his eyes, but nothing happened as General Ironwood took Ozpin's seat.

"Hello Mr. Arc, I'm General Ironwood from Atlas. Do you know why I have come here today?" He had no clue. Jaune was desperate as he picked through his mind to find what kind of trouble he could be in.

"I...have no idea sir."

"Let me make this easier. It has come to my attention that you have met a young lady named Penny, is that correct?" Jaune's ears perked up at the name Penny. He knew it, Penny was some princess and he was about to be arrested for trying to flirt with royalty. It sounded like a scenario from some book, but Jaune's mind was running wild.

"Y-yes sir, I met Penny the other day in Vale." Ironwood pulled out a small box of cigars and lit it with a box of matches that had Junior's club on it. He offered one to Jaune, but he shook his head in fear.

"I'm not here to hurt you Mr. Arc, I just want to talk. It has come to my attention that Penny is very fond of you. However I don't trust others easily." Ironwood puffed away on his cigar, a small circle of smoke smashed into Jaune's face and he coughed.

"We're just really good friends sir, I swear," Jaune said with a small laugh, a laugh of terror.

"You can prove all of this to me later Mr. Arc at dinner tomorrow night. Penny did invite you to dinner did she not?" Ironwood gave a small smirk. Jaune grabbed his scroll and flipped to the message, showing Ironwood.

"Sounds like her, please just remember Mr. Arc, Penny means a lot to me. So when you come over tomorrow night, I expect you to be on your best behavior. We wouldn't want something to happen to you right?" Ironwood folded his hands in the shape of a tent, his eyes stared into Jaune, now a little boy cowering in fear.

"O-of course, I would never do anything to hurt her. You can expect a respectful huntsman tomorrow night!" Jaune stood up and saluted out of instinct. Ironwood nodded in approval and crushed his cigar on an ash tray that happened to appear on Ozpin's desk.

"I'm glad we had this conversation Mr. Arc. You look tired by the way, you should get some rest. Don't dress in a tuxedo, formal wear is fine." Ironwood made his way for the door and patted Jaune on the back. Jaune felt shivers down his spine and lowered his head.

The door closed and Jaune relaxed into the chair, his heart beating so fast that he swore it plopped onto Ozpin's desk during his interrogation. Jaune had no idea what he stumbled into, but now he had no choice, he couldn't abandon the date, or it would upset Penny, and if Penny was upset, so was the general.

As much as he hated to admit, he would need help in preparing for his date with Penny. Date...that word rang through Jaune's head, and he hadn't expected his first actual date to go like this. Jaune needed the best casual wear he could think of, so he decided to ask Weiss, and when it came to acting cool, Ren would be the best in that department.

"James didn't scare you too much did he Mr. Arc?" Ozpin asked as he reentered his office. Jaune jumped in surprised and forgot he was still here.

"No sir, I'm just a little anxious about the whole thing."

"Don't worry too much, James talks a big game, but inside he's soft as a bunny. The only advice I can give you is to have a good time, and act natural. If you do that Mr. Arc, James will treat you with respect." Jaune did not expect Ozpin to go into detail about General Ironwood, especially his relationship with the man.

"I'll do that sir, but I probably should get going." Jaune stood up and made his way out, his legs still shaking from his encounter. Sure Ozpin might know the man more than Jaune, but he had a feeling his many threats were real. If he was going to survive tomorrow night, he would need a plan of action.

"Go get her Mr. Arc," Ozpin said with a giggle.

When he reached his dorm, he was bombarded by both teams, lying in wait for him to return. Ruby and Nora were bouncing on the beds like maniacs, twirling in circles while in fits of laughter. Yang shot up and zoomed over to the door, to prevent his escape, while Pyrrha assured him, that no harm would come to him.

"Ok spill Jaune, what did Ozpin want?" Weiss demanded. A large ruler appeared, and she slapped it in her hand, glaring at Jaune for a reply. All Jaune could do was gulp as Ruby and Nora grabbed his arms like a prisoner.

"Nothing happen guys. Ozpin just wanted me to meet a friend of his, no big deal." Weiss slapped the ruler on her desk, and shook her head in disappointment.

"You're lying to us Jaune, and we don't like liars," Weiss whispered.

"Ren, Pyrrha, please help me!" Ren snapped his head from his book and shrugged. Pyrrha sat next to Blake and held a soft smile.

"Sorry, Jaune, but I too am curious," Pyrrha said.

Yang was up next, and she snatched the ruler from Weiss and made her way over to Jaune. She traced it along his chest and up to his chin, a look of excitement in her bright lilac eyes. She purred in his ears and he began to sweat from embarrassment. Jaune was beginning to regret having these girls as friends.

"If you are telling the truth, then tell us who Ozpin's friend was? We saw an awful lot of military airships out there vomit boy, so it had to be someone pretty important." Yang raised the ruler back a bit, the wood targeting his shin. Jaune had no choice but to tell the truth.

"Alright, alright, just don't beat me please." Yang nodded, and Ruby and Nora let the defenseless boy go. Jaune dusted off his armor and went over to his bed to sit down. He was about to tell quite the story.

"His name was General Ironwood, and he wanted to talk to me about Penny. She's related to him I guess. He will be with her when I attend the dinner tomorrow night, kind of like a chaperone, only worse." Jaune gave out large sigh and threw himself back onto his bed.

"Aw, that's it, thought it would be better." Yang said with a pout.

"No its not, if I mess up this date, he's going to kill me. Probably enlist me into the Atlas army and force me onto the front lines somehow (not that any war is in progress)." Everyone gave a small chuckle except Ruby. She had to find out if Jaune knew Penny's secret.

"We'll help anyway we can Jaune," Pyrrha assured him.

"Can you guys help me find some clothes?"

"I think we can find something," Yang snickered.

Weiss, Yang, and Blake left team JNPR's room, in search of the best outfit that Jaune could wear for his big night with Penny. Ruby trailed behind the trio, but made sure to lie in wait for her to ambush Jaune. She had to find out. If he didn't know she was a real girl, he might take things too far. Not that Ruby thought that would it happen, it was more of a precaution to be honest.

"Ren, can you teach me to talk to girls by tomorrow?" Nora and Pyrrha shot their heads at Ren, an awkward silence filling the room. Ren gave a sigh and slammed his book shut. Ren knew it was going to be a long night.

"I'm not much of an expert, but I can try." Ren jumped down from his bed and propped Pyrrha in front of him. She gave an innocent wave and Jaune began to fiddle with his fingers, a little nervous to practice on the warrior.

For the next several hours, Jaune went through several exercises on how to properly talk with a woman. Simple etiquette and common sense were drilled into his head by Ren and Nora. Every time he gave an inappropriate response, Nora would smack him on the head with the ruler left in their room. The whole thing was embarrassing for Jaune, and he often mumbled his words and made mistakes.

There was progress, Jaune was beginning to learn the "game", that's what Ren called it. Confidence was the key, but not the way Jaune had displayed it earlier in the year on Weiss. Jaune had to not be cocky, and at the same time be his true self, not some made up macho-man.

When night finally approached and the shattered moon came into view, Ren decided to call it a night. He had nothing else to teach Jaune, not that he was really teaching him, since all of his tips were well known in the male population. However Jaune was different, he was awkward and secluded, an innocent boy who knew not much of females.

"I don't know how to thank you Ren," Jaune said, while he rubbed his head of the knots Nora made with her ruler. When everyone was asleep he planned to snap it in half, perhaps hide the pieces.

"Only you can help yourself Jaune, just act calm."

"Yeah, thanks for putting up with me Pyrrha."

"It was no problem Jaune, I found the experience enlightening," Pyrrha mumbled with a blush. Pyrrha couldn't remember the last time a boy had talked to her that way. Everyone was so intimidated by her, so she enjoyed the practice session with Jaune.

"Well it's getting late guys. I'm going to grab my weapon. I forgot it in the cafeteria during all the excitement. I Just hope no one stole it...knowing my luck there buried in the Forever Fall."

Before Jaune could make his way down the hall to absorb his thoughts on the long day, he was ambushed by Ruby, who pounced on him like a tiger hunting its prey. Jaune was tackled onto the floor, with Ruby on top of him. She held a smile of confidence, proud of herself for succeeding in her mission, until she noticed their rather unique position.

"It's nice to see you to Ruby," Jaune rubbed his cheek where a large hand shaped bruise had been left.

"Sorry Jaune, gut reaction. That's not why I tackled you though. I wanted to ask you a question about Penny." The slap mark magically disappeared and Jaune straightened up. It seemed like everyone was asking about Penny.

"Uh, sure, what's up?"

"Have you ever noticed anything weird about her?" It was a general question, but Ruby had no idea how to approach the topic without sounding weird or suspicious.

"Well, she is quite awkward, but I find that cute." Ruby began to blush when she thought about herself. She too had been known to be really strange.

"You never said I was cute!"

"I-I...what about Penny is strange to you?" Jaune diverted the question with a blush. Ruby made sure to confront him later.

"Nothing, I just wanted to know if you really liked her. It's not like she's a robot right?" Ruby said with a nervous laugh. She wanted to punch herself in the face for that last remark. Ruby was never known to be subtle, much less keep a secret so huge.

"You're silly Ruby. Of course she's not a robot."

"Well duh, I mean if I knew a robot I would totally tell you Jaune. Not that I know a robot, I'm just saying you know?" Ruby was stuttering, and spat her words out like a machine gun. Jaune just thought it was Ruby acting her silly self and shrugged.

"I got to get going, I need to find my weapons. It's going to be a long day tomorrow. Don't worry so much about Penny, Ruby. I know what kind of girl she is, trust me." Jaune patted her on the shoulder and raced off to the cafeteria.

"If only you really knew Jaune, if only you knew." Ruby scratched her head and sulked back to her room, her mission was unsuccessful. Jaune would figure it out sooner than later, and she had to make sure their relationship would not be taken to the next level.

Ruby felt bad about ruining their time together, but Jaune happened to pick the wrong girl. Not because she was rude, or horrible, but because of her circumstances. She couldn't help but wonder if there was another reason she was doing this, some subconscious reasoning behind the sabotage. She shook the thought from her head and skipped along.


	4. Product Testing

When a Man Meets a Robot

By wildstraydog

Chapter four: Product Testing

**Thanks everyone for the support, I'm glad a Penny and Jaune story is getting good reception. I hope you all enjoy the next chapter. I got some tips from some of the reviews which I appreciate. Please read and review like always, it inspires me, and RWBY belongs to Rooster Teeth and Monty Oum.**

It was 5:00, and dinner was in two hours. Jaune was beyond nervous, he was afraid for his life. General Ironwood would be there, making sure there were no mistakes. His first date would be a life threatening experience, and it wasn't how he pictured a night with a girl.

For the fifth time Jaune inspected his clothes, twirling around like a girl admiring her dress. He wore a white button up and a brown jacket with a red crest on the right, and a blue tie with stars on it. Jaune had long khaki pants and two new loafers he bought with some of his saved up money. He tried his best to avoid dipping into his savings, but a first date seemed important enough to him.

Not taking any chances, Jaune showered two times today, and sprayed some fancy cologne. Ren lent Jaune some hair gel to spread in his hair, which felt cold and weird at first, he didn't understand the appeal it had on girls, but he wasn't one to judge. Jaune almost fell backwards when he heard the door to his dorm open, and the rest of team JNPR entered with wide eyes.

"Oh wow Jaune, you are quite handsome today." Pyrrha said with a small blush. She was proud of Jaune, he had earned his first date, and he was growing up fast.

"Oh my gosh Jaune looks amazing, I remember Ren looked like this once, it was on a Friday, a young girl had just asked him out, but he never went on dates, hey do you think sloths go on dates?" The three of them just ignored Nora's tirade as Jaune sat down on the bed and gave a nervous sigh.

"Relax Jaune, you'll do fine," Ren said.

"I don't think you understand the pressure I'm experiencing right now. Not only am I nervous about my date, but I'm afraid of dying a horrible death by the hands of Atlas' famous general." They all chuckled at Jaune.

Pyrrha set one of her soft hands on his shoulder. "You worry too much Jaune, just act yourself, and I'm sure the General will like you." Jaune gave a small smile. Pyrrha always had a way of cheering him up.

His scroll hit 5:30, Jaune needed to get ready for the airship. He got up and thanked his teammates who wished him good luck, and made his way downstairs to the front of Beacon, but not before being ambushed by team RWBY. Jaune wasn't surprised. Of course they would want to see him before he left.

"Look at that lady killer ladies, you clean up nice Jaune," Yang gave a small purr and inspected Jaune like a new car, looking him up and down while cupping her chin, nodding in approval.

Blake pushed Yang aside. "Ignore Yang, you look nice Jaune." He gave another blush, and then watched as Weiss walked over, a red tinge gracing her white cheeks.

"For once you look very presentable," Weiss said. "You should always put forth such effort." Weiss darted her eyes and walked away, heading back up to her room while Yang gave a snicker.

"Where's Ruby?"

"I don't know, she said she was busy." Jaune was little disappointed, and he really wanted to show off his new suit to the little girl. Ruby had been acting strange last night, asking weird questions and stuttering, but he couldn't figure out why, maybe she was just worried about Penny.

"Well I better get going, I have to try and survive the trip into Vale." Jaune gave a nervous bow and ran to the airship, only to be greeted again by a little rose-colored girl standing by the docks with a nervous look. Jaune was glad to see Ruby see him off, but she was acting weird again, bouncing back and forth, and then pacing in circles.

"I'm glad I caught you Jaune."

"Yeah no problem, what's up?"

Ruby tried to hide her small blush. "I...just wanted to wish you good luck. Tell me how it goes with Penny. I haven't seen her in a while." Jaune ruffled her hair and she gave a small pout.

"Thanks, I'll tell ya how it goes. You know you're cute when you're all nervous like that," Jaune said with a wink. Ruby gave a large blush and watched as Jaune marched to his death into the airship, already feeling queasy to his stomach.

Ruby was now conflicted more than ever before. Jaune had just called her cute, why would he do that, no boy had ever done that. Jaune was the first true friend she ever made at Beacon, she never thought about him as anything else. Sure Yang would tease her, but she always laughed it off. But now...she was confused, she needed to talk to Yang about it, regardless of the awful jokes about to surface.

She watched as the airship began to lift off, catching Jaune in one of the windows waving, before dipping over with his mouth covered, running to a trash can in one of the corners. Ruby only shook her head at how embarrassing he could be, but it was still funny. When she turned around she ran into Yang and fell backwards, a large mischievous smile graced her lips.

"Sending Jaune off huh, pretty bold of you."

"Oh Yang, I was just worried about Penny is all," Ruby said, careful to form her words without stuttering.

"Sure there isn't something you want to tell me?" Yang helped Ruby up and nudged her in the shoulder. Ruby shook her head back and forth and rushed past Yang, still unsure of when to tell her about her confused feelings, if ever.

The trip to Vale was the longest trip Jaune had ever taken. His head was bent over a trashcan the entire time, his sense of time lost, until the intercom announced they were arriving in two minutes. If Ironwood saw him like this, he would never let him live it down. Penny would give it no mind and probably say something quirky, he liked that about her.

The ship came to a stop and docked at the ports of Vale, and Jaune jumped up in joy as his stomach began to settle. When he made his way down the ramp, he was greeted by two soldiers in red and blue armor, waiting beside a limo with a card that read "Mr. Arc", he felt embarrassed when he raised his hand. The red soldier threw the card and motioned him over.

"Are you Mr. Arc?"

"Y-yeah, I'm supposed to meet General Ironwood." Jaune rubbed the back of his head, extreme fear beginning to enter his system.

The blue soldier opened the door. "Get in, he's expecting you." Jaune got into the limo and sat in the back next to the red soldier, and he noticed the weapons on his waist. Was Ironwood already sending a warning he thought?

The drive to the apartment was quiet and awkward, and the blue soldier kept glancing at him like some prisoner. Jaune heard the red soldier driving give a small chuckle and the silence was broken. It surprised him even further when they began to inquire.

"So what's the deal kid, you're dating Penny?" The red soldier asked.

"W-well, this would actually be my first date with her." The blue soldier smiled, and leaned on his shoulder like they were pals.

"First date huh? I remember my first date, and beer. Man she was smoking, met in her the capital of Atlas, boy did we hit it off," The soldier began to reminiscence. "We hit the club, and well you could say things got a little hot afterwards." Both soldiers laughed and gave a mental high five.

"Penny huh, she can be real special kid." The red soldier said.

"Do y-you guys have any advice about Ironwood?" The car was silent again, and the blue soldier gave a small cough. Jaune couldn't believe how scary the man could be, his mere name shaking the will of his soldiers.

"All I can recommend is don't do anything stupid," The blue soldier said. "Looks like you won't have to wait to find out." The limo came to a stop in front of a large apartment complex. It was large orange tinge building with columns that stood over thirty stories tall. Jaune couldn't believe he didn't remember a building so tall when he last came to visit Vale.

The soldiers led Jaune to the elevator and pushed the 30th floor button. Ironwood had the special lot on the top of the building reserved for the entire Vytal festival. It was the best place to accommodate Penny. During the short elevator ride, the red soldier began to hum a quiet little song while his friend tapped his fingers against the wall. Jaune found it a little funny how casual they could be.

The doors opened, and a large hall with one door came into view. On the front door, a poorly drawn picture of Penny and Ironwood in crayon hung like a sign reading, "Penny and Ironwood's Super Fun Place", which made Jaune snicker. The red soldier rang the doorbell and they stood at attention on either side.

"Good job boys, I'll take Mr. Arc from here." They both saluted and Jaune gave a big gulp as he walked into castle Ironwood.

The apartment was beyond beautiful, leaving Jaune's mouth agape. The walls were painted in a cerulean blue, and a soft purple carpet accompanied by beautiful paintings of famous war heroes from the Great War. Jaune saw a small garden on the balcony, with fresh tomatoes and peppers beginning to show life, and a fireplace near the couch. He almost slammed into a large bust of a famous general from Atlas until he stopped it from shaking.

"I see you like the apartment Mr. Arc, do you like Atlesian art?" Ironwood led him to another painting of the large snow covered mountains found in Atlas, and Jaune nodded, impressed by the work.

"It's very nice sir. What will we be having for dinner tonight?" Ironwood led him to the table and they both sat down in the mahogany chairs with red grooves dancing around the sides.

"We will be having a nice cuisine dinner, and Penny should be also done in her room soon. She wanted to make sure she looked nice enough." When Ironwood finished his sentence, Jaune felt a large glare and aura begin to surrounded him, and Ironwood's face read "You better compliment her or else", and Jaune nodded in discreet understanding.

"Here I am Uncle Ironwood," an enthusiastic female voice screamed. Penny skipped into the common air and beamed at Jaune's presence.

Jaune held a small blush that he tried to hide as he looked at Penny's dress. She wore a large white skirt with red ribbons attached, with a red top that glistened in the light thanks to the glitter, and a blue bow nestled on her short ginger-colored hair. Penny was wearing some long white gloves and red ruby sleepers, that Jaune thought looked expensive.

"Y-you l-look beautiful Penny," Jaune mumbled.

"Oh wow thank you Jaune that is so stupendous of you!" Penny said as she hopped over to her seat across from Jaune with a large smile gracing her lips. She picked up the silverware on the table and began to clash them together in anticipation, while Ironwood gave a sigh.

Ironwood took out a cigar and lit it. "Before we begin our meal Mr. Arc, I would think it would be appropriate if you told us more about you." Ironwood waved the match and threw it across the large glass table, giving a few large puffs his way.

"Oh that would be swell Jaune. I would like to learn more about you." Penny was playing with her napkin as she stuffed it in her lap while bobbing her head to an imaginary tune in her head.

"Um, sure, well I come from a small village with seven other sisters. I belong to the famous Arc family, but I'm sure you knew that already, and I'm a team leader at Beacon Academy." Jaune twiddled with his fingers as he told them some basic information, Ironwood's steel expression unfazed.

"Team leader huh, Ozpin must have seen a lot of potential in you Mr. Arc. Are you participating in the tournament, Penny will be there with her team."

"Penny has a team?" Jaune couldn't believe it, the sweet innocent looking girl, who was more awkward then Jaune was a huntress? Well it wasn't that surprising, after all he already knew six other beautiful looking girls that could kick plenty of ass.

"Oh yes Jaune, I am combat ready!" Penny shouted, flexing her arms. Jaune could only give a small chuckle as Penny tried to look strong.

"Penny is quite the fighter Jaune...you best watch yourself in the tournament." Jaune became frightened again, the way Ironwood said the sentence sent a chill down his spine, and he looked at Penny as he tilted her head and waved. Jaune was beginning to think there might be more to the little girl then meets the eye, especially if Ironwood trained her.

"I haven't seen any of her teammates around, have they not arrived in Vale yet?"

"Not yet, they should be arriving within a few days though. I brought Penny early with me because she wanted to visit Vale before the tournament began," Ironwood explained. "She's been having a good time, and she got to you meet you." Jaune didn't know if he should take that as compliment, but he nodded and said thanks.

"Its dinner time," Penny yelled after a small beep was heard in the kitchen. Ironwood got up and smashed his cigar on an ashtray that somehow appeared on the table. When Ironwood disappeared Penny reached over the table and whispered to Jaune.

"After dinner, can we go into town?"

"Yeah sure, but what about your uncle," Jaune began to sweat at the thought of Ironwood beginning a manhunt across Vale, groups of soldiers scouring through bushes.

"You leave uncle Ironwood to me." Penny gave a large mischievous smile and sat back down, as Ironwood brought their meals.


	5. A Slight Malfunction

When a Man Meets a Robot

By wildstraydog

Chapter Five: A Slight Malfunction

**I'm back guys with another adventure of Jaune and Penny. We got to get these reviews up guys, and I need more motivation and thoughts. I would also like to thank everyone who has read my other story as well, I really appreciate it. Also, I'm looking for some cover art for this story, so if anyone has any suggestions please let me know. RWBY is owned by Rooster Teeth and Monty Oum.**

"Hey dude," the blue soldier asked. The both of them were still standing guard in front of the apartment, both bored out of their mind.

"What's up?"

"Ever wonder why we're here?"

"It's one of life's great mysteries, isn't it? Why are we here? I mean, are we the product of some... cosmic coincidence? Or is there really a God, watching everything, you know, with a plan for us and stuff. I don't know man, but it keeps me up at night."

"What...I mean why are we here, standing guard in front of this apartment just for a date," The blue soldier said confused at his teammate's answer.

"Um...yeah," Red said.

"What was all that stuff about God? Do you want to talk about it?" The blue soldier scratched the back of his head, trying to clear up the awkward moment between them. It was the strangest thing he ever seen.

"Nah...I'm ok. How much longer you think we have?"

"Beats me man," Blue said.

Back inside the apartment, Jaune, Penny, and Ironwood enjoyed their meals in silence. Penny was trying her best to mimic good table manners, while Jaune stole a few glances at Penny, without Ironwood noticing. For a first date, it was really strange. Jaune still didn't know what Penny was planning to get rid of Ironwood so they could escape, so he just sat back and waited.

Ironwood was about to say something, but his scroll began to beep, and he stood up. Ironwood walked away from the table and took the call, while Penny held back a small little chuckle that Jaune found cute. By the way she was acting it was obvious that this was part of her master plan. Jaune didn't know why he felt scared, but something about her concocting a plan made him shudder.

"I understand," Ironwood mumbled in anger. He walked back to the table and stared Jaune down. Jaune felt a little bit of his soul get crushed to pieces by a trash compacter and then thrown under a bulldozer.

"What's wrong uncle?" Penny said with a weird tone, but Ironwood wasn't able to catch the act, too caught in his head with the situation.

"Someone tried to hack the system, they need me there to monitor the situation," Ironwood said with a defeated sigh. "Mr. Arc, I trust you to behave yourself and take care of Penny. I'll be leaving my soldiers here to make sure you two are safe." Jaune gave a scared nod and Ironwood took his leave, the two soldiers saluted him and he left.

Penny tried her best to suppress the glee, but she jumped up in the air and pumped her fists. She began to do a little dance, and Jaune tried not to laugh. Despite the circumstances he still found her adorable. Jaune also took note that he would have to teach Penny how to dance one day.

"Phase 1 of 'operation getaway' has been initiated!" Penny yelled. Jaune waved his arms to settle her down, in case the soldiers heard her outside. "Oh don't worry Jaune I have a plan for those two as well." Penny gave a forced wink, and walked over to the door.

"What do you plan on doing?"

"I've been around them awhile Jaune, they can be easily distracted." Penny placed her hand on the door and closed her eyes. Unknown to Jaune, Penny was scanning the outside room, calculating chances of success, and the auras of the lazy soldiers. A probability popped up inside her mind and she stood back from the door with a large smile.

Penny turned around and had Jaune huddle like a football team planning their next play. "Ok Jaune, here's the plan. You're going to go outside and distract them for a bit, while I pretend to be Ironwood and send them on some crazy mission." Jaune nodded and rolled his eyes, he had a few reservations about the plan.

"Um, Penny, what am I going to talk about, and how do you plan on sounding like Ironwood, you two sound nothing alike." Penny broke the huddle and pointed her thumb at her chest, and shouted.

"Don't worry about me. I'm more talented than I look." Jaune gave a small snicker at her attempt to sound confident, and she began to laugh with him. Jaune gave a sigh and walked toward the door, preparing himself for his act that he had to put on. Penny urged him to go out and hopped up and down. Jaune had to learn how to resist women.

He opened the door and the soldiers turned their heads in surprise at Jaune and relaxed. The blue soldier waltzed over and put his arm around Jaune, snickering behind his helmet. Jaune knew whatever he was thinking wasn't kid friendly.

"I hear you got the apartment alone with Penny, this is your big chance kid." Jaune began to blush, and the red soldier walked over to separate them.

"Alright, give the kid a break, it's his first date."

"Well, actually guys, I need some advice about Penny." They both looked at Jaune and blinked behind their helmets, not expecting Jaune to ask them for dating advice. They both didn't want to admit it, but they weren't Casanova's either. Red had seen Blue on a couple of dates, but they always ended in disaster. Red hadn't gone on a date in years since he joined the military.

"What kind of advice?" Red asked.

"I mean, what does Penny like to do," Jaune said with a stutter. "Like in her free time, I just want to know more about her really." Both soldiers cupped their chins and began to think back on their interactions with the girl.

"Penny likes making friends and video games," Blue said.

"Video games huh..." The soldiers were snapped out of their trance when both of their scrolls began to beep, Red answered first and saw the image of Ironwood staring at him with a disappointed look. Red knew that look, it meant he and his partner were about to go through hell.

"I have a new mission for you two, its urgent."

"Yes sir," they said in unison.

"I've decided to get Penny a pet, I want you both to search the pet shops of Vale and pick the perfect dog or cat." The soldiers turned to look at each other and scratched their heads, until they saw Ironwood begin to glare. They locked up and saluted.

"Something's not right here..." The red soldier said.

"We shouldn't question the General, remember last time we questioned one of his orders?" They both looked up in the air and began to shudder, an unpleasant memory filling both their heads.

The soldiers took the exit out of the building and left in a hurry, leaving Jaune silent, a look of disbelief in his eyes. He was beginning to think they were some of the stupidest soldiers he had ever met, which would explain why they were standing guard at their date. Jaune vowed he would never fall for such a simple trick as long as he lived.

"Are they gone?" Penny peeked out the door and darted her eyes back and forth with a smile plastered on her face. Jaune nodded and she burst out the door. She ran over to Jaune and grabbed his hand.

"So, what do we do now, it was your plan after all?"

"..." Penny stared at Jaune with a blank face, a smile still on her lips, processing what course of action to take next. Her mind began to calculate what sort of activities young boys like to participate in. She thought of video games, racing, sports, and action movies.

"Actually there's this pretty cool arcade we could go to." Penny looked up and beamed. She loved to play video games, all the problem solving, and simulation battles. However she felt strange today, and when she looked down, Penny noticed she was still holding Jaune's hand. Penny didn't know how to describe how she felt at that moment.

The warmth of his hand, felt strange on her cool metallic ones, and she felt a small blush reach her cheeks. Even if she wasn't a real girl, something about holding Jaune's hand felt significant and special. Penny already knew the ramifications about holding hands with a boy, and the implied signals it could send to Jaune. When she looked up, she saw Jaune was a little flustered and nervous.

"That would be positively fabulous Jaune!" Penny said with glee. She dragged Jaune into the elevator and pushed the bottom-floor button like a child. Jaune tried to hold back his laughter and watched as Penny bobbed her head.

Let it be known that even though the idea of going to an arcade in Vale seemed like an amazing idea to Jaune, he never thought about what time it was. When they exited the apartment he realized it was night, and he looked at the scroll to see it was 6:30 PM. His face went pale, but Penny dragged his lifeless body.

Penny had already figured out the location of the arcade in her head, but she noticed that Jaune seemed upset. Penny thought it might be him being shy, and continued to drag him through the streets, with a few couples whispering at how strange the pair was. Jaune didn't realize in his bout of silence that they passed two familiar characters eating at a ramen shop, one with blue hair and the other a monkey tail.

"Yo, Sun, isn't that Jaune?" Neptune asked.

Sun slurped down some noodles and twisted around in his chair. "Hey, you're right that is Jaune, and he's with a girl?" they both began to laugh, while Sun came up with a brilliant idea.

"I thought he liked Weiss," Neptune said. "That's what it always looked like anyway. Hey are you ok Sun?" Neptune saw Sun digging through his pants, pulling out his scroll. Sun tapped away at some buttons and gave a sinister smile.

"The girls will get a kick out of this, let's record the whole thing!" Neptune laughed, but his smile faded at Sun's lack of respect for privacy.

"Nah, just leave them alone, you know how Jaune is."

"Hmm, you're probably right...damn it would have been great too. Wait, I have a better idea Neptune, one that will help Jaune. Yeah it will be perfect." Neptune titled his head and saw Sun rubbing his hands together like some maniacal villain in the shadows.

"And that plan is...?"

"What if we follow them, not to spy, but to see how Jaune is doing," Sun explained. "You know how shy that boy can be, we can give him some pointers, help nudge the date along, make it successful." Neptune cupped his chin and thought about Sun's crazy plan, it not being the first in a long line of crazy schemes he had thought up.

"Aw come on Neptune, it's our duty as bros!" Neptune gave a sigh and nodded his head.

"Ok ok, fine. But we got to make sure we don't do anything to ruin their date, I mean it Sun. We have to remain hidden, only talk to Jaune through your scroll or behind an alley or something." They both high-fived and set out to help their fellow man, Jaune unaware that he had gained two allies that night in his pursuit for happiness.

At the arcade, Jaune was surprised to see that it was still open, the sign reading "open till ten". It was really suspicious to him. Jaune had never heard of an arcade staying open until 10:00, what kind of kids were still out playing video games that late anyway? He threw common sense to the side and entered with Penny, hands still embraced.

Penny was in video game overload, darting her eyes at every different machine with flashing lights and joysticks. In the corner she saw a cool looking FPS game that pit super-soldiers against Grim, and she dragged Jaune over to play the game. Jaune fished around in his pockets to find some spare Lien and popped them in the machine.

"Do you know how to play Penny?" Jaune never asked if Penny had any experience with games, but if the soldiers were telling the truth she had some appreciation for them at the least. Penny's eyes became still, and she read the instructions that blared across the screen.

In lightening fast movements, Penny began the game and swung the joysticks around, clearing the levels like a professional gamer, blasting away the grim on-screen. Jaune's mouth was agape as he watched the sweet innocent girl, become a video game killing machine. With the first level cleared, Penny broke a high score and turned around to jump in joy with Jaune who just blinked.

"Wow Penny...you're amazing, you have to teach me!"

"Sure Jaune, it's real simple." Jaune took his place at the machine and began the second level, Penny hovering over his shoulder, excited to teach him. In the corner, Neptune and Sun watched with smiles on their faces. Sun pulled out his scroll and brought up Jaune's contact info, ready to message him at the right opportunity.

"It's time to turn Jaune into Romeo."


	6. Recall of Wingmen

When a Man Meets a Robot

By wildstraydog

Chapter Six: Recall of Wingmen

** Hey guys I'm back with another adventure. I've decided to alternate between short and long chapters with this story so I don't lose my creative groove. I understand if this might upset people, so please read and review, we need to crank those up by the way. RWBY belongs to Rooster Teeth and Monty Oum.**

A small beeping noise broke Jaune's thoughts from Penny who was dancing gracefully in the corner on the arcade game, _Dance like you're Crazy. _She was great if not better then he was. Jaune reminded himself to ask her where she learned her moves after fiddling with his scroll. Sun's picture appeared on a mini screen and he tilted his head, confused why Sun of all people would be calling him today.

Jaune cleared his throat, "Uh, hello?"

"There's our Romeo, how ya doing Jaune," Sun yelled into his scroll with excitement. "I and Neptune couldn't help but notice you actually found a girl to go on date with you, good job man!" Jaune wanted to sink into the floor like a puddle of mud-embarrassed that Sun and Neptune caught them in Vale...he could already hear the stories.

"So...why did you call sun," Jaune said with a flat sigh. The only way he would survive this day was if he cooperated now.

"Whoa man chill out, we ain't going to ruin your date, in fact we're here to help you out." Jaune's back straightened out and he checked if Penny noticed anything strange. He was glad to see she was still preoccupied with the dancing game on some new hardcore experience. Boy was she fast with her legs Jaune thought.

"H-help m-me, how do you plan on doing that?"

"Just listen to what we have to say ok, follow my cue." Sun sounded calm and confident, and Jaune did notice he had a way with the women, and Neptune even impressed Weiss on his first try (something he still resented). So deciding he had nothing to lose came easy.

"Alright...what do I do?"

"Sounds like you want to impress her right, so here's what were going to do. Neptune is going to put on a mask and pretend to scare her," Sun began to explain. "And then you jump in and say some brave words, yada, yada, yada, and she'll be swooning all over you!" Jaune's thoughts of how impressed he was with Sun and Neptune began to dwindle. What sort of half-assed conquest was this?

"Sun...I think you've been watching too much TV. That will never work, especially for a girl like Penny." Jaune saw Penny complete the level with a new high score, and she jumped up and down in glee, turning to rush over to Jaune with a large smile.

"Just head outside ok," Sun yelled before hanging up. There was no choice now-the plan had been set in motion, if you could call it that Jaune thought. There was no way she was going to fall for this, and Penny was strong...too strong for a normal teenage girl. There was a good chance Neptune could end up with a few broken ribs.

"Jaune, it was fantastic, I beat the highest score on that machine over there, and all you had to do was dance, how amazing is that?" Penny said with wonder in her eyes. She noticed the nervous look on Jaune and tilted her head, but smiled and snapped her fingers.

"Jaune, might you want to tell me something?"

"Well, actually yes, how did you learn to dance like that?"

Penny nodded, "I was pro-I mean taught to do many things Jaune. You could say I'm deck of cards filled with aces. Well that's what uncle Ironwood says anyway..." Jaune scratched his chin and laughed, he was learning something new about this girl every day.

"Hey, how about we head for the carnival in town, there only here for a couple of days I hear..." Jaune had been to carnivals with his sisters many times, and it was always a hassle being dragged around to each ride and mini-game to endure their wrath. The thought of going with a girl on a date excited him.

Penny stayed silent, not saying a word for a few minutes, only closing her eyes as she thought, while in truth shifting through files on carnivals. Uncle Ironwood had never taken her to such events, so it was something new to her. Although she had seen some information about couples going to carnivals to have fun: eating cotton candy, riding the Ferris wheel, going into the tunnel of love.

"Jaune...that sounds...absolutely splendid, let's go." She cheered, running past Jaune to the exit. He smiled and rush after Penny, only then remembering a second later about the plan Sun had set up with Neptune.

"Stop right there miss and give me your money," Neptune popped out from around the corner, wearing a cheesy white mask with straps and a phony accent to accompany it. Jaune face palmed at the fact that he didn't even bother to change his clothes. It was official. They were the worst wingmen ever. Ren would be ten times better.

"Oh no, bandits Jaune," Penny gasped. She was about to enter combat mode and attack the nefarious bandit, until Jaune stepped forward, covering Penny like a knight straight from a medieval portrait. To any other girl, it would appear like an gold aura surrounded him, the heavens opening up, but to Penny, she was just amazed at his calm demeanor in the face of danger.

"Stand back foul stranger Or I'll smite you." Jaune wanted to vomit right there at his horrible choice of lines. Why was he talking like some old coot? Neptune was trying his best to hold back his laughter, but straightened up and continued his role as a robber.

"Darn you brave Hunter, if only you weren't here, I shall retreat to the shadows!" Neptune pulled out a small shard of dust and threw it on the ground, filling the front of the arcade in smoke.

Sun watched from above to see the results, worried at the silence Penny held. Jaune turned around to see her smiling, shaking with...joy? No, that couldn't be right sun thought. She should be scared, and jumping into Jaune's arms like a scared little cat (not that Blake would ever do that).

"How thoughtful of you Jaune to protect me, but I can take care of myself if it happens again. After all I am combat ready!" Penny squealed. She grabbed Jaune's hands, leading them into the streets, the both of them headed for the carnival as Sun slunk back defeated.

"Well that didn't work out," Neptune mused.

"We're going to need some backup..." Sun pulled out his scroll and pulled up a picture of Blake. The scroll rang for a few seconds and she answered.

"Hey Blake, its sun...can I talk to Yang?"


End file.
